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Between Christmas and New Year’s is always a great time to get away, but for most folks, it’s to a warm, sunny beach in the Caribbean. Not us! We decided we would spend New Year’s Eve in Lisbon and then rent a car and tour the countryside for a few days.

We began our trip in Lisbon, flying in and easily taking the subway to our hotel. From there, we began exploring the city, which was easy as it’s easily navigable, but also a bit hilly. From the city center, there were several directions we could take… one of my favorites was meandering up the hillside to the Castelo de Sao Jorge, which overlooks the city. The winding hike up the hillside takes you through such a wide variety of iconic tile-faced homes, with a beautiful yet rustic look. Street art is quite plentiful in Lisbon, as well as on the various meandering streets as we hiked up.

Working our way back down the hill, we passed a variety of bakeries offering Pao de Natal, a culinary favorite from Portugal that is basically a creamy creme brule in a small pastry cup. They were everywhere this time of year, as were the street cars taking people up and down the various hills in Lisbon, reminiscent of San Francisco.

The next day was New Year’s Eve, so we decided to walk through the various small streets of Bairro Altos, where we found a restaurant (Tapa Bucho Gastrobar) serving a special New Year’s Eve menu that was to die for! After dinner, we found our way to one of several small gay bars in the area. Between this area and some surrounding neighborhoods one can find a wide variety of gay bars, including bear bars and more.

The next day, we found ourselves back down in the center of Lisbon, where we took a different direction to the Time Out Marketplace, full of a wide variety of food stands offering culinary delights from all corners of Portugal. It’s tough to decide on what to choose, but we settled on a few breaded cod dishes, as well as some pork, and washed it all down with one of the wide variety of Portuguese wines found all throughout Lisbon.

After lunch, we walked along the hills to find a few vantage points in the western part of the city, so that we could take some stunning photos of the sun setting, with its long shadows hitting the eastern Lisbon hillside just right!

The next day started our road trip, and just outside of Lisbon is the fairytale town of Sintra, set in mountains and hills just west of the city and overlooking the ocean. Sintra is a truly magical place, holding on to its original medieval architecture and small, winding streets. Above Sintra is an old Moorish fortification one can see from miles away, and just above that is the Pena Palace, which is the only castle we’ve ever personally been through that makes you feel like you’re strolling the castle walkways the way they did hundreds of years ago. The castle, having been restored after earthquakes in years past, is a photographic icon of Portugal, with its orange and red-painted walls and Moorish flair, including artistic tile work, all along the way.

The next day we arrived in Porto, Portugal’s 2nd largest city and a UNESCO World Heritage site. Porto is such a throwback to an earlier time, and its wealth from those centuries is depicted in the gorgeous Gothic buildings and fortifications found on the walk down to the waterfront.

From Porto, we did a road trip up the Duoro River and found the Quinto Do Bomfim winery along the way. I always thought port wine was strictly sweet, but no… we found some incredible dry white ports to taste, as well as some complex reds. Needless to say, we bought a few bottles for the rest of our trip, and then had a late lunch in the town of Pinhao.

From here, we decided to road trip south, first stopping in the town of Aveiro, reminiscent of the Venice canals, for some coffee. That evening, we were in the Algarve region in the south, and decided to stay at the Casa Risa gay guest house tucked away near the small town of Lagos. This turned out to be a great way to wind down our trip, as the owner made us not only feel right at home during the entire stay… he even invited us out with some locals for a special Kings Day (Dia de Reis) dinner at Restaurant A Curva just down the street. Between this dinner and the rest of our stay, there was no port wine bottles left in our stash!

As a side note, for our next trip to Lisbon, the folks at Casa Risa recommended we stay at Villa 3 Caparica, just south of the city. From what we found online, it looked like a perfect urban compliment to the Casa Risa.

We did enjoy a few outdoor cafe meals in the Algarve, as well as our drive down to some of the beautiful local beaches, with some being known as “gay beaches” and some nude. It was too chilly in January for too many people to be down there, but there were a few. We continued on to check out the Fortaleza de Sagres and the dramatic Portuguese coastline, alongside fisherman fishing from the cliff tops and dropping their line over a hundred feet below. I never did see anyone catch a fish!

This wrapped up our trip this time around… we drove back to Lisbon for our flight home. Road tripping, by the way, is incredibly easy, as the drive from Porto to the south was about 5 hours. Of course, the train is very convenient throughout the country as well.

Matt Skallerud and Richard Brower enjoy eating well and traveling more! They met while they were both an active part of the IGLTA team, and are married and now live in New York City. Richard’s talents are finding incredible flight deals from JFK to points all over the world, as well as locating the best eateries along the way. Matt is part of Pink Banana Media, Pink Banana World and the #ILoveGay network, and enjoys merging his personal and professional worlds along the way on these trips.